U.S. Pat. No. 3,281,475 disclosed a process for forming diethers of polyethylene glycol by reacting tertiary olefins with monoalkyl ethers of polyethylene glycol in the presence of an anhydrous, macroreticular, resinous, polysulfonic acid. Some olefins could not be used in the process. For example, secondary olefins such as propylene and cyclohexene did not react at all or reacted to such a slight extent that it was not possible to detect their formation (column 5, lines 25-37). The products formed nonionic surface active agents which were highly resistant to alkali.
In U.S. Pat. No. 4,187,384 a similar process was disclosed utilizing C.sub.3-5 alkenes further identified as including propylene and other n-olefins or isobutene (column 2, lines 39-47). There was no disclosure that C.sub.5-6 cyclic alkenes could be utilized according to the described process. It was also taught that high yields of the desired product were obtained only by lowering the temperature of the reaction to a final temperature of from 40.degree. C. to 80.degree. C. The products formed were useful as aprotic solvents and extractants and as hydraulic fluids.